Diphenylmethane Property

Melting point:

22-24 °C (lit.)

Boiling point:

264 °C (lit.)

Density 

1.006 g/mL at 25 °C (lit.)

vapor density 

5.79 (vs air)

vapor pressure 

<1 mm Hg ( 77 °C)

refractive index 

n20/D 1.577(lit.)

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

Soluble in ethanol, ether, benzene and chloroform.

pka

33.5(at 25℃)

form 

Low Melting Solid

Specific Gravity

1.006

color 

Colorless to pale yellow

Odor

at 10.00 % in dipropylene glycol. sweet green wet plastic geranium

Odor Type

green

explosive limit

0.69-8.66%(V)

Water Solubility 

14.1mg/L(25 ºC)

FreezingPoint 

24.0 to 26.0 ℃

Merck 

14,3328

BRN 

1904982

Dielectric constant

2.6（26℃）

LogP

4.140

CAS DataBase Reference

101-81-5(CAS DataBase Reference)

NIST Chemistry Reference

Diphenylmethane(101-81-5)

EPA Substance Registry System

Diphenylmethane (101-81-5)

Safety

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25-58-54-44-29

RIDADR 

UN3077

WGK Germany 

2

RTECS 

DA4976500

Autoignition Temperature

905 °F

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29029090

Hazardous Substances Data

101-81-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2250 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

Diphenylmethane Chemical Properties,Usage,Production

Definition

Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH2Ph2). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as benzhydryl, and it is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride.

Uses

Diphenylmethane is widely used in the synthesis of luminogens for aggregation-induced emission (AIE).
It is used in the preparation of a polymerization initiator, diphenylmethyl potassium (DPMK).
It is one of the precursors in the synthesis of a dendrimeric polycyclic aromatic hydrocarbon (PAH), hexakis[4-(1,1,2-triphenyl-ethenyl)phenyl]benzene.

Application

The main application of diphenylmethane includes widely used in the synthesis of luminogens for aggregation-induced emission (AIE) and used in the preparation of a polymerization initiator, diphenylmethyl potassium (DPMK). It is one of the precursors in the synthesis of a dendrimeric polycyclic aromatic hydrocarbon (PAH), hexakis [4-(1,1,2-triphenyl-ethenyl) phenyl] benzene.

Synthesis

The classical synthesis of Diphenylmethane (DPMK) is the indirect metallation via potassium naphthenide. n-Butyllithium (n-BuLi) solution (1.6 M in hexanes) and sec-butyllithium (sec-BuLi) solution (1.4 M in cyclohexane) were diluted and ampoulized on a high vacuum line. Lithium chloride (99.999%, LiCl,) was dried at 130 °C for 2 days and then diluted to the target concentration in THF and ampoulized under a reduced pressure of 10-6 mm Hg. Sodium (NaNaph) and potassium naphthalenide (K-Naph) were prepared by the reaction of the corresponding metal with naphthalene in THF at room temperature for 48 h. Diphenyl methyl potassium (DPMK) was prepared by the reaction of K-Naph with diphenylmethane in THF under high vacuum conditions at room temperature for 72 h. The concentration of DPMK was determined by titration using octyl alcohol and used for anionic polymerization. All initiators were sealed off under high vacuum into ampoules with break seals and stored at -30 °C.

Chemical Properties

Colorless to pale yellow low melting solid

Occurrence

Has apparently not been reported to occur in nature.

Uses

Diphenylmethane, is used as an adhesive chemical composition for making flexible laminates for use in food packaging.

Preparation

By interaction of benzyl chloride and benzene in the presence of an acid cata lyst.

Definition

ChEBI: A diarylmethane that is methane substituted by two phenyl groups.

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 5663, 1969 DOI: 10.1021/ja01048a053
Chemical and Pharmaceutical Bulletin, 27, p. 2405, 1979 DOI: 10.1248/cpb.27.2405
The Journal of Organic Chemistry, 57, p. 2143, 1992 DOI: 10.1021/jo00033a041

Metabolism

Diphenylmethane is hydroxylated in the rabbit and some 15% of the dose is excreted as 4-hydroxydiphenylmethane, which is largely (80-90%) in the free state. Neither the hydrocarbon nor its metabolite is oestrogenic. This reaction also occurs in the dog (Williams, 1959).

Purification Methods

Sublime it under vacuum, or distil it at 72-75o/0.4mm. Recrystallise it from cold EtOH. It has also been purified by fractional crystallisation from the melt. [Armarego Aust J Chem 13 95 1960, Beilstein 5 II 498, 5 IV 1841.]